Chemical Examination of Citrus sinensis Flavedo Variety Pineapple
Identifieur interne : 000A33 ( Pmc/Corpus ); précédent : 000A32; suivant : 000A34Chemical Examination of Citrus sinensis Flavedo Variety Pineapple
Auteurs : Geeta Rani ; Lalita Yadav ; S. B. KalidharSource :
- Indian Journal of Pharmaceutical Sciences [ 0250-474X ] ; 2009.
Abstract
Phytochemical examination of
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DOI: 10.4103/0250-474X.59552
PubMed: 20376223
PubMed Central: 2846475
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<record><TEI><teiHeader><fileDesc><titleStmt><title xml:lang="en">Chemical Examination of <italic>Citrus sinensis</italic> Flavedo Variety Pineapple</title><author><name sortKey="Rani, Geeta" sort="Rani, Geeta" uniqKey="Rani G" first="Geeta" last="Rani">Geeta Rani</name><affiliation><nlm:aff id="AF0001">Department of Chemistry and Physics, CCS Haryana Agricultural University, Hisar - 125 004, India</nlm:aff></affiliation></author><author><name sortKey="Yadav, Lalita" sort="Yadav, Lalita" uniqKey="Yadav L" first="Lalita" last="Yadav">Lalita Yadav</name><affiliation><nlm:aff id="AF0001">Department of Chemistry and Physics, CCS Haryana Agricultural University, Hisar - 125 004, India</nlm:aff></affiliation></author><author><name sortKey="Kalidhar, S B" sort="Kalidhar, S B" uniqKey="Kalidhar S" first="S. B." last="Kalidhar">S. B. Kalidhar</name><affiliation><nlm:aff id="AF0001">Department of Chemistry and Physics, CCS Haryana Agricultural University, Hisar - 125 004, India</nlm:aff></affiliation></author></titleStmt><publicationStmt><idno type="wicri:source">PMC</idno><idno type="pmid">20376223</idno><idno type="pmc">2846475</idno><idno type="url">http://www.ncbi.nlm.nih.gov/pmc/articles/PMC2846475</idno><idno type="RBID">PMC:2846475</idno><idno type="doi">10.4103/0250-474X.59552</idno><date when="2009">2009</date><idno type="wicri:Area/Pmc/Corpus">000A33</idno></publicationStmt><sourceDesc><biblStruct><analytic><title xml:lang="en" level="a" type="main">Chemical Examination of <italic>Citrus sinensis</italic> Flavedo Variety Pineapple</title><author><name sortKey="Rani, Geeta" sort="Rani, Geeta" uniqKey="Rani G" first="Geeta" last="Rani">Geeta Rani</name><affiliation><nlm:aff id="AF0001">Department of Chemistry and Physics, CCS Haryana Agricultural University, Hisar - 125 004, India</nlm:aff></affiliation></author><author><name sortKey="Yadav, Lalita" sort="Yadav, Lalita" uniqKey="Yadav L" first="Lalita" last="Yadav">Lalita Yadav</name><affiliation><nlm:aff id="AF0001">Department of Chemistry and Physics, CCS Haryana Agricultural University, Hisar - 125 004, India</nlm:aff></affiliation></author><author><name sortKey="Kalidhar, S B" sort="Kalidhar, S B" uniqKey="Kalidhar S" first="S. B." last="Kalidhar">S. B. Kalidhar</name><affiliation><nlm:aff id="AF0001">Department of Chemistry and Physics, CCS Haryana Agricultural University, Hisar - 125 004, India</nlm:aff></affiliation></author></analytic><series><title level="j">Indian Journal of Pharmaceutical Sciences</title><idno type="ISSN">0250-474X</idno><idno type="eISSN">1998-3743</idno><imprint><date when="2009">2009</date></imprint></series></biblStruct></sourceDesc></fileDesc><profileDesc><textClass></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en"><p>Phytochemical examination of <italic>Citrus sinensis</italic> flavedo var. Pineapple resulted in the isolation of six compounds characterized as tetracosane, ethyl pentacosanoate, tetratriacontanoic acid, tangertin, β-sitosteryl-β-D-glucoside and 3,5,4'-trihydroxy-7,3'-dimethoxy flavanone 3-O-β-glucoside. Of these 3,5,4'-trihydroxy-7,3'-dimethoxy flavanone 3-O-β-glucoside is a hitherto unreported compound.</p></div></front><back><div1 type="bibliography"><listBibl><biblStruct><analytic><author><name sortKey="Bakshi, Gdn" uniqKey="Bakshi G">GDN Bakshi</name></author><author><name sortKey="Sensarama, P" uniqKey="Sensarama P">P Sensarama</name></author><author><name sortKey="Pal, Dc" uniqKey="Pal D">DC Pal</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Kirtikar, Kr" uniqKey="Kirtikar K">KR Kirtikar</name></author><author><name sortKey="Basu, Bd" uniqKey="Basu B">BD Basu</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Ramachandran, S" uniqKey="Ramachandran S">S Ramachandran</name></author><author><name sortKey="Anbu, J" uniqKey="Anbu J">J Anbu</name></author><author><name sortKey="Saravanan, M" uniqKey="Saravanan M">M Saravanan</name></author><author><name sortKey="Gnanasam" uniqKey="Gnanasam">Gnanasam</name></author><author><name sortKey="Sridhar, Sk" uniqKey="Sridhar S">SK Sridhar</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Barbara, Nt" uniqKey="Barbara N">NT Barbara</name></author><author><name sortKey="Hoffmann, Jj" uniqKey="Hoffmann J">JJ Hoffmann</name></author><author><name sortKey="Jolad, Sd" uniqKey="Jolad S">SD Jolad</name></author><author><name sortKey="Bates, Rb" uniqKey="Bates R">RB Bates</name></author><author><name sortKey="Siahaan, Tj" uniqKey="Siahaan T">TJ Siahaan</name></author></analytic></biblStruct></listBibl></div1></back></TEI><pmc article-type="other"><pmc-dir>properties open_access</pmc-dir>
<front><journal-meta><journal-id journal-id-type="nlm-ta">Indian J Pharm Sci</journal-id><journal-id journal-id-type="publisher-id">IJPhS</journal-id><journal-title-group><journal-title>Indian Journal of Pharmaceutical Sciences</journal-title></journal-title-group><issn pub-type="ppub">0250-474X</issn><issn pub-type="epub">1998-3743</issn><publisher><publisher-name>Medknow Publications</publisher-name><publisher-loc>India</publisher-loc></publisher></journal-meta><article-meta><article-id pub-id-type="pmid">20376223</article-id><article-id pub-id-type="pmc">2846475</article-id><article-id pub-id-type="publisher-id">IJPhS-71-677</article-id><article-id pub-id-type="doi">10.4103/0250-474X.59552</article-id><article-categories><subj-group subj-group-type="heading"><subject>Short Communication</subject></subj-group></article-categories><title-group><article-title>Chemical Examination of <italic>Citrus sinensis</italic> Flavedo Variety Pineapple</article-title></title-group><contrib-group><contrib contrib-type="author"><name><surname>Rani</surname><given-names>Geeta</given-names></name><xref ref-type="aff" rid="AF0001"></xref></contrib><contrib contrib-type="author"><name><surname>Yadav</surname><given-names>Lalita</given-names></name><xref ref-type="aff" rid="AF0001"></xref></contrib><contrib contrib-type="author"><name><surname>Kalidhar</surname><given-names>S. B.</given-names></name><xref ref-type="aff" rid="AF0001"></xref><xref ref-type="corresp" rid="cor1">*</xref></contrib></contrib-group><aff id="AF0001">Department of Chemistry and Physics, CCS Haryana Agricultural University, Hisar - 125 004, India</aff><author-notes><corresp id="cor1"><label>*</label><bold>Address for correspondence</bold> E-mail: <email xlink:href="sbkalidhar@gmail.com">sbkalidhar@gmail.com</email></corresp></author-notes><pub-date pub-type="ppub"><season>Nov-Dec</season><year>2009</year></pub-date><volume>71</volume><issue>6</issue><fpage>677</fpage><lpage>679</lpage><history><date date-type="received"><day>06</day><month>4</month><year>2009</year></date><date date-type="rev-recd"><day>24</day><month>8</month><year>2009</year></date><date date-type="accepted"><day>27</day><month>11</month><year>2009</year></date></history><permissions><copyright-statement>© Indian Journal of Pharmaceutical Sciences</copyright-statement><copyright-year>2009</copyright-year><license license-type="open-access" xlink:href="http://creativecommons.org/licenses/by/2.0/"><license-p>This is an open-access article distributed under the terms of the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.</license-p></license></permissions><abstract><p>Phytochemical examination of <italic>Citrus sinensis</italic> flavedo var. Pineapple resulted in the isolation of six compounds characterized as tetracosane, ethyl pentacosanoate, tetratriacontanoic acid, tangertin, β-sitosteryl-β-D-glucoside and 3,5,4'-trihydroxy-7,3'-dimethoxy flavanone 3-O-β-glucoside. Of these 3,5,4'-trihydroxy-7,3'-dimethoxy flavanone 3-O-β-glucoside is a hitherto unreported compound.</p></abstract><kwd-group><kwd><italic>Citrus sinensis</italic></kwd><kwd>Rutaceae</kwd><kwd>tetracosane</kwd><kwd>ethyl pentacosanoate</kwd><kwd>tetratriacontanoic acid</kwd><kwd>tangertin</kwd><kwd>β-sitosteryl-β-D-glucoside</kwd><kwd>3,5,4'-trihydroxy-7,3'-dimethoxy flavanone 3-O-β-glucoside</kwd></kwd-group></article-meta></front><body><p><italic>Citrus sinensis</italic> (L.) Osbeck var. Pineapple (syn, C. <italic>aurantium</italic> L. var. <italic>sinensis)</italic> belongs[<xref ref-type="bibr" rid="CIT1">1</xref>] to Rutaceae family and it is commonly known as sweet orange or <italic>mosambi</italic>. Its fruit is strengthening[<xref ref-type="bibr" rid="CIT2">2</xref>], cardiotonic, laxative, anthelmintic and removes fatigue. It possesses[<xref ref-type="bibr" rid="CIT3">3</xref>] antiinflammatory and antioxidant properties. A survey of literature showed that this variety had not been subjected to chemical analysis so far and the present investigation had therefore been undertaken.</p><p>Melting points were determined on Ganson Electrical Melting Point Apparatus. <sup>1</sup>H NMR spectra were recorded on Bruker AC-400F MHz NMR Spectrometer in CDCI<sub>3</sub> using TMS as internal standard. IR spectra were obtained on Perkin Elmer Infrared Spectrophotometer. Mass spectra were recorded on VG-70S 11-250J GC-MS-DS Mass Spectrometer.</p><p>Fruits (15 kg) of this plant were collected from Department of Horticulture, CCSHAU, Hisar. Flavedos (outer part of peel) were chopped into small pieces and then extracted with hot methanol. The solvent was removed to obtain extractives. The extractives were concentrated on a water bath under reduced pressure to obtain a viscous mass. The viscous mass thus obtained was mixed with silica gel (60-120 mesh), dried on water bath and subjected to silica gel (60-120 mesh) column chromatography and six compounds were isolated which were characterized as tetracosane (A), ethyl pentacosanoate (B), tetratriacontanoic acid (C), tangertin (D), β-sitosteryl-β-D-glucoside (E), 3,5,4'-trihydroxy-7,3'-dimethoxy flavanone 3-O-β-glucoside (<xref ref-type="fig" rid="F0001">Fig. 1</xref>). Of these, 3,5,4'-trihydroxy-7,3'-dimethoxy flavanone 3-O-β-glucoside is a hitherto unreported compound.</p><fig id="F0001" position="float"><label>Fig. 1</label><caption><p>Structures of new compounds from Citrus sinensis 1a: 3,5,4'-trihydroxy-7,3'-dimethoxy flavanone, 1b: 3,5,4'-trihydroxy- 7,3'-dimethoxy flavanone 3-O-β-glucoside</p></caption><graphic xlink:href="IJPhS-71-677-g001"></graphic></fig><p>Compound F (3,5,4'-trihydroxy-7,3'-dimethoxy flavanone 3-O-β-glucoside, (1b) obtained on elution with methanol-ethyl acetate (1:9) and it crystallized out from ethyl alcohol, 85 mg, m.p. 210°. It responded to Mg/HCl test. Alcoholic FeCl<sub>3</sub> gave brown colour. Found 56.07, H 5.26; C<sub>23</sub>H<sub>26</sub>O<sub>12</sub> requires C 55.87, H 5.26 %. UV λ<sub>max</sub> (nm) 250, 287 (MeOH); 250, 287 (MeOH+NaOAc), 250, 311 (MeOH+AlCl<sub>3</sub>); 250, 311 (MeOH+AlCl<sub>3</sub>+HCl). IR ν<sub>max</sub> (nujol, cm<sup>−1</sup>): 815, 975, 1070, 1095, 1131, 1202, 1278, 1358, 1443, 1518, 1607, 1647, 2918, 3471. MS (m/z): 494 (M<sup>+</sup>, 3), 464 (8), 463 (27), 446 (12), 418 (33), 386(36), 374 (41), 330 (100), 214 (38), 159 (5), 158 (16), 134 (3), 132 (10), 102 (6). Molish test: positive. Kiliani hydrolysis: glucose, confirmed by direct comparison using paper chromatography. Aglycone: UV λ<sub>max</sub> (nm) 250, 288 (MeOH); 250, 288 (MeOH+NaOAc); 250, 310 (MeOH+AlCl<sub>3</sub>); 250, 310 (MeOH+AlCl<sub>3</sub>+HCl). Acetate of glycoside: Ac<sub>2</sub>O/Py, m.p. 144°. <sup>1</sup>H NMR of glycoside acetate (δ, CDCl<sub>3</sub>): 2.04, 2.06, 2.07, 2.09 (3H each, 4s, 4*OAc); 2.32, 2.38 (3H each, 2s, 2*OAc); 2.70-5.50 (9 H, m, 2 C- ring protons, 7 glucose protons); 3.87 (6 H, s, 2*OMe); 6.31 (1H,<italic>J</italic> 2.5 Hz, H-6); 6.46 (1H, <italic>J</italic> 2.5 Hz, H-8); 7.01 (1H, <italic>J</italic> 7.5 Hz, H-5'); 7.15 (1H, d, <italic>J</italic> 2.5 Hz, H-2'); 7.26 (1H, dd, <italic>J</italic> 7.5 Hz, 2.5 Hz., H-6').</p><p>The brown colour with alcoholic ferric chloride indicated it to be a phenolic compound. The positive Mg/HCl colour reaction suggested it to be a flavonoid. IR depicted the presence of CO (1647 cm<sup>−1</sup>) and OH (3471 cm<sup>−1</sup>) groups. Elemental analysis indicated its molecular formula: C<sub>23</sub>H<sub>26</sub>O<sub>12</sub> and molecular mass: 494. Its acetate was prepared by using acetic anhydride and pyridine. The <sup>1</sup>H NMR of the acetate in CDCl<sub>3</sub> showed a double doublet (<italic>J</italic> 7.5, 2.5 Hz) at δ 7.26, integrating to one proton, which could be H-6' of a flavanone. A doublet (<italic>J</italic> 2.5 Hz) was observed at δ 7.15, integrating to one proton, which could be H-2'. Another doublet (<italic>J</italic> 7.5 Hz.) was observed at δ 7.01, integrating to one proton, indicating it to be H-5'. There was a doublet (<italic>J</italic> 2.5 Hz.) at δ 6.46, integrating to one proton, which could be H-8. A doublet (<italic>J</italic> 2.5 Hz) at δ 6.31, for one proton, could be due to H-6. There was a singlet at δ 3.87, integrating to six protons, indicating two methoxy groups in the compound. There was a multiplet for nine protons in the range δ 2.70 - 5.50 and these could be seven protons of glucose and two protons of the C - ring of a flavanone. A singlet at δ 2.38, integrating to three protons, indicated a phenolic acetoxyl. Another singlet for second phenolic acetoxyl group was observed at δ 2.32. Four alcoholic acetoxyls at δ 2.09 (3H), 2.07(3H), 2.06 (3H), 2.04 (3H) indicated the presence of glucose in the molecule. This data suggested compound F to be 3,5,7,3',4'-pentaoxygenated flavanone-O-glucoside.</p><p>The original compound showed bathochromic shift with AlCl<sub>3</sub>/HCl hinting the presence of 5-OH in the compound F. The addition of sodium acetate did not show bathochromic shift in the UV-Vis of the glycoside and aglycone hinting the presence of 7-OMe in the both. The aglycone of the flavanone could be one of the following three, (i) 3,5,3'-trihydroxy-7,4'-dimethoxy (ii) 3,5,4'-trihydroxy-7,3'-dimethoxy (iii) 5,3',4'-trihydroxy-3,7-dimethoxy. The aglycone, obtained after Kiliani hydrolysis, had properties identical to (ii). The aglycone could therefore be settled as 3,5,4'-trihydroxy-7,3'-dimethoxy flavanone (1-a)[<xref ref-type="bibr" rid="CIT4">4</xref>].</p><p>The compound F could be one of the following two (i) 3,5,4'-trihydroxy-7,3'-dimethoxy flavanone 4'-O-glucoside (ii) 3,5,4'-trihydroxy-7,3'-dimethoxy flavanone-3-O-glucoside. The positions of H-5' in the acetates of compound F and that in 3,5,4'-trihydroxy-7,3'-dimethoxy flavanone are comparable; δ 7.01 in the former and δ 7.07 in the latter[<xref ref-type="bibr" rid="CIT4">4</xref>]; hinting that both have 4'-OH. The compound F could therefore be settled as 3,5,4'-trihydroxy-7,3'-dimethoxy flavanone 3-O-β-D- glucoside, (1 b).</p></body><back><ack><p>The authors are grateful to Horticulture Department, Haryana Agricultural University, for providing us the plant material; and thank SAIF, PU, Chandigarh for the spectral data.</p></ack><fn-group><fn fn-type="other"><p><bold>Rani <italic>et al</italic>.: Chemical components of <italic>Citrus sinensis</italic></bold></p></fn></fn-group><ref-list><title>REFERENCES</title><ref id="CIT1"><label>1</label><element-citation publication-type="book"><person-group person-group-type="author"><name><surname>Bakshi</surname><given-names>GDN</given-names></name><name><surname>Sensarama</surname><given-names>P</given-names></name><name><surname>Pal</surname><given-names>DC</given-names></name></person-group><source>A Lexicon of Medicinal Plants in India</source><year>1999</year><publisher-loc>Calcutta</publisher-loc><publisher-name>Naya Prokash</publisher-name></element-citation></ref><ref id="CIT2"><label>2</label><element-citation publication-type="book"><person-group person-group-type="author"><name><surname>Kirtikar</surname><given-names>KR</given-names></name><name><surname>Basu</surname><given-names>BD</given-names></name></person-group><source>Indian Medicinal Plants</source><year>1984</year><volume>Vol 2</volume><publisher-loc>Dehradun</publisher-loc><publisher-name>Singh and Singh</publisher-name></element-citation></ref><ref id="CIT3"><label>3</label><element-citation publication-type="journal"><person-group person-group-type="author"><name><surname>Ramachandran</surname><given-names>S</given-names></name><name><surname>Anbu</surname><given-names>J</given-names></name><name><surname>Saravanan</surname><given-names>M</given-names></name><name><surname>Gnanasam</surname></name><name><surname>Sridhar</surname><given-names>SK</given-names></name></person-group><article-title>Antioxidant and antiinflammatory properties of <italic>Citrus sinensis</italic> peel extract</article-title><source>Indian J Pharm Sci</source><year>2002</year><volume>64</volume><fpage>66</fpage><lpage>8</lpage></element-citation></ref><ref id="CIT4"><label>4</label><element-citation publication-type="journal"><person-group person-group-type="author"><name><surname>Barbara</surname><given-names>NT</given-names></name><name><surname>Hoffmann</surname><given-names>JJ</given-names></name><name><surname>Jolad</surname><given-names>SD</given-names></name><name><surname>Bates</surname><given-names>RB</given-names></name><name><surname>Siahaan</surname><given-names>TJ</given-names></name></person-group><article-title>Diterpenoids and flavonoids from <italic>Grindelia discoidea</italic></article-title><source>Phytochem</source><year>1986</year><volume>25</volume><fpage>723</fpage><lpage>7</lpage></element-citation></ref></ref-list></back></pmc></record>Pour manipuler ce document sous Unix (Dilib)
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